diff --git a/agent/skill_commands.py b/agent/skill_commands.py
index 76bd204d59..b9d5135fd5 100644
--- a/agent/skill_commands.py
+++ b/agent/skill_commands.py
@@ -14,6 +14,110 @@ logger = logging.getLogger(__name__)
 _skill_commands: Dict[str, Dict[str, Any]] = {}
 
 
+def _load_skill_payload(skill_identifier: str, task_id: str | None = None) -> tuple[dict[str, Any], Path | None, str] | None:
+    """Load a skill by name/path and return (loaded_payload, skill_dir, display_name)."""
+    raw_identifier = (skill_identifier or "").strip()
+    if not raw_identifier:
+        return None
+
+    try:
+        from tools.skills_tool import SKILLS_DIR, skill_view
+
+        identifier_path = Path(raw_identifier).expanduser()
+        if identifier_path.is_absolute():
+            try:
+                normalized = str(identifier_path.resolve().relative_to(SKILLS_DIR.resolve()))
+            except Exception:
+                normalized = raw_identifier
+        else:
+            normalized = raw_identifier.lstrip("/")
+
+        loaded_skill = json.loads(skill_view(normalized, task_id=task_id))
+    except Exception:
+        return None
+
+    if not loaded_skill.get("success"):
+        return None
+
+    skill_name = str(loaded_skill.get("name") or normalized)
+    skill_path = str(loaded_skill.get("path") or "")
+    skill_dir = None
+    if skill_path:
+        try:
+            skill_dir = SKILLS_DIR / Path(skill_path).parent
+        except Exception:
+            skill_dir = None
+
+    return loaded_skill, skill_dir, skill_name
+
+
+def _build_skill_message(
+    loaded_skill: dict[str, Any],
+    skill_dir: Path | None,
+    activation_note: str,
+    user_instruction: str = "",
+) -> str:
+    """Format a loaded skill into a user/system message payload."""
+    from tools.skills_tool import SKILLS_DIR
+
+    content = str(loaded_skill.get("content") or "")
+
+    parts = [activation_note, "", content.strip()]
+
+    if loaded_skill.get("setup_skipped"):
+        parts.extend(
+            [
+                "",
+                "[Skill setup note: Required environment setup was skipped. Continue loading the skill and explain any reduced functionality if it matters.]",
+            ]
+        )
+    elif loaded_skill.get("gateway_setup_hint"):
+        parts.extend(
+            [
+                "",
+                f"[Skill setup note: {loaded_skill['gateway_setup_hint']}]",
+            ]
+        )
+    elif loaded_skill.get("setup_needed") and loaded_skill.get("setup_note"):
+        parts.extend(
+            [
+                "",
+                f"[Skill setup note: {loaded_skill['setup_note']}]",
+            ]
+        )
+
+    supporting = []
+    linked_files = loaded_skill.get("linked_files") or {}
+    for entries in linked_files.values():
+        if isinstance(entries, list):
+            supporting.extend(entries)
+
+    if not supporting and skill_dir:
+        for subdir in ("references", "templates", "scripts", "assets"):
+            subdir_path = skill_dir / subdir
+            if subdir_path.exists():
+                for f in sorted(subdir_path.rglob("*")):
+                    if f.is_file():
+                        rel = str(f.relative_to(skill_dir))
+                        supporting.append(rel)
+
+    if supporting and skill_dir:
+        skill_view_target = str(skill_dir.relative_to(SKILLS_DIR))
+        parts.append("")
+        parts.append("[This skill has supporting files you can load with the skill_view tool:]")
+        for sf in supporting:
+            parts.append(f"- {sf}")
+        parts.append(
+            f'\nTo view any of these, use: skill_view(name="{skill_view_target}", file_path="<path>")'
+        )
+
+    if user_instruction:
+        parts.append("")
+        parts.append(f"The user has provided the following instruction alongside the skill invocation: {user_instruction}")
+
+    return "\n".join(parts)
+
+
 def scan_skill_commands() -> Dict[str, Dict[str, Any]]:
     """Scan ~/.hermes/skills/ and return a mapping of /command -> skill info.
 
@@ -83,77 +187,60 @@ def build_skill_invocation_message(
     if not skill_info:
         return None
 
-    skill_name = skill_info["name"]
-    skill_path = skill_info["skill_dir"]
+    loaded = _load_skill_payload(skill_info["skill_dir"], task_id=task_id)
+    if not loaded:
+        return f"[Failed to load skill: {skill_info['name']}]"
 
-    try:
-        from tools.skills_tool import SKILLS_DIR, skill_view
+    loaded_skill, skill_dir, skill_name = loaded
+    activation_note = (
+        f'[SYSTEM: The user has invoked the "{skill_name}" skill, indicating they want '
+        "you to follow its instructions. The full skill content is loaded below.]"
+    )
+    return _build_skill_message(
+        loaded_skill,
+        skill_dir,
+        activation_note,
+        user_instruction=user_instruction,
+    )
 
-        loaded_skill = json.loads(skill_view(skill_path, task_id=task_id))
-    except Exception:
-        return f"[Failed to load skill: {skill_name}]"
 
-    if not loaded_skill.get("success"):
-        return f"[Failed to load skill: {skill_name}]"
+def build_preloaded_skills_prompt(
+    skill_identifiers: list[str],
+    task_id: str | None = None,
+) -> tuple[str, list[str], list[str]]:
+    """Load one or more skills for session-wide CLI preloading.
 
-    content = str(loaded_skill.get("content") or "")
-    skill_dir = Path(skill_info["skill_dir"])
+    Returns (prompt_text, loaded_skill_names, missing_identifiers).
+    """
+    prompt_parts: list[str] = []
+    loaded_names: list[str] = []
+    missing: list[str] = []
 
-    parts = [
-        f'[SYSTEM: The user has invoked the "{skill_name}" skill, indicating they want you to follow its instructions. The full skill content is loaded below.]',
-        "",
-        content.strip(),
-    ]
+    seen: set[str] = set()
+    for raw_identifier in skill_identifiers:
+        identifier = (raw_identifier or "").strip()
+        if not identifier or identifier in seen:
+            continue
+        seen.add(identifier)
 
-    if loaded_skill.get("setup_skipped"):
-        parts.extend(
-            [
-                "",
-                "[Skill setup note: Required environment setup was skipped. Continue loading the skill and explain any reduced functionality if it matters.]",
-            ]
+        loaded = _load_skill_payload(identifier, task_id=task_id)
+        if not loaded:
+            missing.append(identifier)
+            continue
+
+        loaded_skill, skill_dir, skill_name = loaded
+        activation_note = (
+            f'[SYSTEM: The user launched this CLI session with the "{skill_name}" skill '
+            "preloaded. Treat its instructions as active guidance for the duration of this "
+            "session unless the user overrides them.]"
         )
-    elif loaded_skill.get("gateway_setup_hint"):
-        parts.extend(
-            [
-                "",
-                f"[Skill setup note: {loaded_skill['gateway_setup_hint']}]",
-            ]
-        )
-    elif loaded_skill.get("setup_needed") and loaded_skill.get("setup_note"):
-        parts.extend(
-            [
-                "",
-                f"[Skill setup note: {loaded_skill['setup_note']}]",
-            ]
+        prompt_parts.append(
+            _build_skill_message(
+                loaded_skill,
+                skill_dir,
+                activation_note,
+            )
         )
+        loaded_names.append(skill_name)
 
-    supporting = []
-    linked_files = loaded_skill.get("linked_files") or {}
-    for entries in linked_files.values():
-        if isinstance(entries, list):
-            supporting.extend(entries)
-
-    if not supporting:
-        for subdir in ("references", "templates", "scripts", "assets"):
-            subdir_path = skill_dir / subdir
-            if subdir_path.exists():
-                for f in sorted(subdir_path.rglob("*")):
-                    if f.is_file():
-                        rel = str(f.relative_to(skill_dir))
-                        supporting.append(rel)
-
-    if supporting:
-        skill_view_target = str(Path(skill_path).relative_to(SKILLS_DIR))
-        parts.append("")
-        parts.append("[This skill has supporting files you can load with the skill_view tool:]")
-        for sf in supporting:
-            parts.append(f"- {sf}")
-        parts.append(
-            f'\nTo view any of these, use: skill_view(name="{skill_view_target}", file_path="<path>")'
-        )
-
-    if user_instruction:
-        parts.append("")
-        parts.append(f"The user has provided the following instruction alongside the skill invocation: {user_instruction}")
-
-    return "\n".join(parts)
+    return "\n\n".join(prompt_parts), loaded_names, missing
diff --git a/cli.py b/cli.py
index 13bf4736b4..d696488f23 100755
--- a/cli.py
+++ b/cli.py
@@ -8,6 +8,7 @@ Features ASCII art branding, interactive REPL, toolset selection, and rich forma
 Usage:
     python cli.py                          # Start interactive mode with all tools
     python cli.py --toolsets web,terminal  # Start with specific toolsets
+    python cli.py --skills hermes-agent-dev,github-auth
     python cli.py -q "your question"       # Single query mode
     python cli.py --list-tools             # List available tools and exit
 """
@@ -1043,11 +1044,40 @@ def build_welcome_banner(console: Console, model: str, cwd: str, tools: List[dic
 # Skill Slash Commands — dynamic commands generated from installed skills
 # ============================================================================
 
-from agent.skill_commands import scan_skill_commands, get_skill_commands, build_skill_invocation_message
+from agent.skill_commands import (
+    scan_skill_commands,
+    get_skill_commands,
+    build_skill_invocation_message,
+    build_preloaded_skills_prompt,
+)
 
 _skill_commands = scan_skill_commands()
 
 
+def _parse_skills_argument(skills: str | list[str] | tuple[str, ...] | None) -> list[str]:
+    """Normalize a CLI skills flag into a deduplicated list of skill identifiers."""
+    if not skills:
+        return []
+
+    if isinstance(skills, str):
+        raw_values = [skills]
+    elif isinstance(skills, (list, tuple)):
+        raw_values = [str(item) for item in skills if item is not None]
+    else:
+        raw_values = [str(skills)]
+
+    parsed: list[str] = []
+    seen: set[str] = set()
+    for raw in raw_values:
+        for part in raw.split(","):
+            normalized = part.strip()
+            if not normalized or normalized in seen:
+                continue
+            seen.add(normalized)
+            parsed.append(normalized)
+    return parsed
+
+
 def save_config_value(key_path: str, value: any) -> bool:
     """
     Save a value to the active config file at the specified key path.
@@ -1313,6 +1343,8 @@ class HermesCLI:
         self._command_status = ""
         self._attached_images: list[Path] = []
         self._image_counter = 0
+        self.preloaded_skills: list[str] = []
+        self._startup_skills_line_shown = False
 
         # Voice mode state (also reinitialized inside run() for interactive TUI).
         self._voice_lock = threading.Lock()
@@ -1599,6 +1631,13 @@ class HermesCLI:
     def show_banner(self):
         """Display the welcome banner in Claude Code style."""
         self.console.clear()
+        if self.preloaded_skills and not self._startup_skills_line_shown:
+            skills_label = ", ".join(self.preloaded_skills)
+            self.console.print(
+                f"[bold {_accent_hex()}]Activated skills:[/] {skills_label}"
+            )
+            self.console.print()
+            self._startup_skills_line_shown = True
         
         # Auto-compact for narrow terminals — the full banner with caduceus
         # + tool list needs ~80 columns minimum to render without wrapping.
@@ -5829,6 +5868,7 @@ def main(
     query: str = None,
     q: str = None,
     toolsets: str = None,
+    skills: str | list[str] | tuple[str, ...] = None,
     model: str = None,
     provider: str = None,
     api_key: str = None,
@@ -5853,6 +5893,7 @@ def main(
         query: Single query to execute (then exit). Alias: -q
         q: Shorthand for --query
         toolsets: Comma-separated list of toolsets to enable (e.g., "web,terminal")
+        skills: Comma-separated or repeated list of skills to preload for the session
         model: Model to use (default: anthropic/claude-opus-4-20250514)
         provider: Inference provider ("auto", "openrouter", "nous", "openai-codex", "zai", "kimi-coding", "minimax", "minimax-cn")
         api_key: API key for authentication
@@ -5869,6 +5910,7 @@ def main(
     Examples:
         python cli.py                            # Start interactive mode
         python cli.py --toolsets web,terminal    # Use specific toolsets
+        python cli.py --skills hermes-agent-dev,github-auth
         python cli.py -q "What is Python?"       # Single query mode
         python cli.py --list-tools               # List tools and exit
         python cli.py --resume 20260225_143052_a1b2c3  # Resume session
@@ -5938,6 +5980,8 @@ def main(
         else:
             toolsets_list = ["hermes-cli"]
     
+    parsed_skills = _parse_skills_argument(skills)
+
     # Create CLI instance
     cli = HermesCLI(
         model=model,
@@ -5953,6 +5997,20 @@ def main(
         pass_session_id=pass_session_id,
     )
 
+    if parsed_skills:
+        skills_prompt, loaded_skills, missing_skills = build_preloaded_skills_prompt(
+            parsed_skills,
+            task_id=cli.session_id,
+        )
+        if missing_skills:
+            missing_display = ", ".join(missing_skills)
+            raise ValueError(f"Unknown skill(s): {missing_display}")
+        if skills_prompt:
+            cli.system_prompt = "\n\n".join(
+                part for part in (cli.system_prompt, skills_prompt) if part
+            ).strip()
+            cli.preloaded_skills = loaded_skills
+
     # Inject worktree context into agent's system prompt
     if wt_info:
         wt_note = (
diff --git a/hermes_cli/main.py b/hermes_cli/main.py
index 3d910907d7..c1b60e5822 100644
--- a/hermes_cli/main.py
+++ b/hermes_cli/main.py
@@ -499,6 +499,7 @@ def cmd_chat(args):
         "model": args.model,
         "provider": getattr(args, "provider", None),
         "toolsets": args.toolsets,
+        "skills": getattr(args, "skills", None),
         "verbose": args.verbose,
         "quiet": getattr(args, "quiet", False),
         "query": args.query,
@@ -510,7 +511,11 @@ def cmd_chat(args):
     # Filter out None values
     kwargs = {k: v for k, v in kwargs.items() if v is not None}
     
-    cli_main(**kwargs)
+    try:
+        cli_main(**kwargs)
+    except ValueError as e:
+        print(f"Error: {e}")
+        sys.exit(1)
 
 
 def cmd_gateway(args):
@@ -2276,6 +2281,7 @@ Examples:
     hermes config edit            Edit config in $EDITOR
     hermes config set model gpt-4 Set a config value
     hermes gateway                Run messaging gateway
+    hermes -s hermes-agent-dev,github-auth
     hermes -w                     Start in isolated git worktree
     hermes gateway install        Install as system service
     hermes sessions list          List past sessions
@@ -2314,6 +2320,12 @@ For more help on a command:
         default=False,
         help="Run in an isolated git worktree (for parallel agents)"
     )
+    parser.add_argument(
+        "--skills", "-s",
+        action="append",
+        default=None,
+        help="Preload one or more skills for the session (repeat flag or comma-separate)"
+    )
     parser.add_argument(
         "--yolo",
         action="store_true",
@@ -2349,6 +2361,12 @@ For more help on a command:
         "-t", "--toolsets",
         help="Comma-separated toolsets to enable"
     )
+    chat_parser.add_argument(
+        "-s", "--skills",
+        action="append",
+        default=None,
+        help="Preload one or more skills for the session (repeat flag or comma-separate)"
+    )
     chat_parser.add_argument(
         "--provider",
         choices=["auto", "openrouter", "nous", "openai-codex", "anthropic", "zai", "kimi-coding", "minimax", "minimax-cn"],
diff --git a/tests/agent/test_skill_commands.py b/tests/agent/test_skill_commands.py
index 2e2ac64ccd..42a6fb4d84 100644
--- a/tests/agent/test_skill_commands.py
+++ b/tests/agent/test_skill_commands.py
@@ -4,7 +4,11 @@ import os
 from unittest.mock import patch
 
 import tools.skills_tool as skills_tool_module
-from agent.skill_commands import scan_skill_commands, build_skill_invocation_message
+from agent.skill_commands import (
+    scan_skill_commands,
+    build_skill_invocation_message,
+    build_preloaded_skills_prompt,
+)
 
 
 def _make_skill(
@@ -79,6 +83,33 @@ class TestScanSkillCommands:
         assert "/generic-tool" in result
 
 
+class TestBuildPreloadedSkillsPrompt:
+    def test_builds_prompt_for_multiple_named_skills(self, tmp_path):
+        with patch("tools.skills_tool.SKILLS_DIR", tmp_path):
+            _make_skill(tmp_path, "first-skill")
+            _make_skill(tmp_path, "second-skill")
+            prompt, loaded, missing = build_preloaded_skills_prompt(
+                ["first-skill", "second-skill"]
+            )
+
+        assert missing == []
+        assert loaded == ["first-skill", "second-skill"]
+        assert "first-skill" in prompt
+        assert "second-skill" in prompt
+        assert "preloaded" in prompt.lower()
+
+    def test_reports_missing_named_skills(self, tmp_path):
+        with patch("tools.skills_tool.SKILLS_DIR", tmp_path):
+            _make_skill(tmp_path, "present-skill")
+            prompt, loaded, missing = build_preloaded_skills_prompt(
+                ["present-skill", "missing-skill"]
+            )
+
+        assert "present-skill" in prompt
+        assert loaded == ["present-skill"]
+        assert missing == ["missing-skill"]
+
+
 class TestBuildSkillInvocationMessage:
     def test_loads_skill_by_stored_path_when_frontmatter_name_differs(self, tmp_path):
         skill_dir = tmp_path / "mlops" / "audiocraft"
diff --git a/tests/hermes_cli/test_chat_skills_flag.py b/tests/hermes_cli/test_chat_skills_flag.py
new file mode 100644
index 0000000000..8551b4105a
--- /dev/null
+++ b/tests/hermes_cli/test_chat_skills_flag.py
@@ -0,0 +1,77 @@
+import sys
+
+
+def test_top_level_skills_flag_defaults_to_chat(monkeypatch):
+    import hermes_cli.main as main_mod
+
+    captured = {}
+
+    def fake_cmd_chat(args):
+        captured["skills"] = args.skills
+        captured["command"] = args.command
+
+    monkeypatch.setattr(main_mod, "cmd_chat", fake_cmd_chat)
+    monkeypatch.setattr(
+        sys,
+        "argv",
+        ["hermes", "-s", "hermes-agent-dev,github-auth"],
+    )
+
+    main_mod.main()
+
+    assert captured == {
+        "skills": ["hermes-agent-dev,github-auth"],
+        "command": None,
+    }
+
+
+def test_chat_subcommand_accepts_skills_flag(monkeypatch):
+    import hermes_cli.main as main_mod
+
+    captured = {}
+
+    def fake_cmd_chat(args):
+        captured["skills"] = args.skills
+        captured["query"] = args.query
+
+    monkeypatch.setattr(main_mod, "cmd_chat", fake_cmd_chat)
+    monkeypatch.setattr(
+        sys,
+        "argv",
+        ["hermes", "chat", "-s", "github-auth", "-q", "hello"],
+    )
+
+    main_mod.main()
+
+    assert captured == {
+        "skills": ["github-auth"],
+        "query": "hello",
+    }
+
+
+def test_continue_worktree_and_skills_flags_work_together(monkeypatch):
+    import hermes_cli.main as main_mod
+
+    captured = {}
+
+    def fake_cmd_chat(args):
+        captured["continue_last"] = args.continue_last
+        captured["worktree"] = args.worktree
+        captured["skills"] = args.skills
+        captured["command"] = args.command
+
+    monkeypatch.setattr(main_mod, "cmd_chat", fake_cmd_chat)
+    monkeypatch.setattr(
+        sys,
+        "argv",
+        ["hermes", "-c", "-w", "-s", "hermes-agent-dev"],
+    )
+
+    main_mod.main()
+
+    assert captured == {
+        "continue_last": True,
+        "worktree": True,
+        "skills": ["hermes-agent-dev"],
+        "command": "chat",
+    }
diff --git a/tests/test_cli_preloaded_skills.py b/tests/test_cli_preloaded_skills.py
new file mode 100644
index 0000000000..90fee6cf6a
--- /dev/null
+++ b/tests/test_cli_preloaded_skills.py
@@ -0,0 +1,130 @@
+from __future__ import annotations
+
+import importlib
+import os
+import sys
+from unittest.mock import MagicMock, patch
+
+import pytest
+
+
+def _make_real_cli(**kwargs):
+    clean_config = {
+        "model": {
+            "default": "anthropic/claude-opus-4.6",
+            "base_url": "https://openrouter.ai/api/v1",
+            "provider": "auto",
+        },
+        "display": {"compact": False, "tool_progress": "all"},
+        "agent": {},
+        "terminal": {"env_type": "local"},
+    }
+    clean_env = {"LLM_MODEL": "", "HERMES_MAX_ITERATIONS": ""}
+    prompt_toolkit_stubs = {
+        "prompt_toolkit": MagicMock(),
+        "prompt_toolkit.history": MagicMock(),
+        "prompt_toolkit.styles": MagicMock(),
+        "prompt_toolkit.patch_stdout": MagicMock(),
+        "prompt_toolkit.application": MagicMock(),
+        "prompt_toolkit.layout": MagicMock(),
+        "prompt_toolkit.layout.processors": MagicMock(),
+        "prompt_toolkit.filters": MagicMock(),
+        "prompt_toolkit.layout.dimension": MagicMock(),
+        "prompt_toolkit.layout.menus": MagicMock(),
+        "prompt_toolkit.widgets": MagicMock(),
+        "prompt_toolkit.key_binding": MagicMock(),
+        "prompt_toolkit.completion": MagicMock(),
+        "prompt_toolkit.formatted_text": MagicMock(),
+    }
+    with patch.dict(sys.modules, prompt_toolkit_stubs), patch.dict(
+        "os.environ", clean_env, clear=False
+    ):
+        import cli as cli_mod
+
+        cli_mod = importlib.reload(cli_mod)
+        with patch.object(cli_mod, "get_tool_definitions", return_value=[]), patch.dict(
+            cli_mod.__dict__, {"CLI_CONFIG": clean_config}
+        ):
+            return cli_mod.HermesCLI(**kwargs)
+
+
+class _DummyCLI:
+    def __init__(self, **kwargs):
+        self.kwargs = kwargs
+        self.session_id = "session-123"
+        self.system_prompt = "base prompt"
+        self.preloaded_skills = []
+
+    def show_banner(self):
+        return None
+
+    def show_tools(self):
+        return None
+
+    def show_toolsets(self):
+        return None
+
+    def run(self):
+        return None
+
+
+def test_main_applies_preloaded_skills_to_system_prompt(monkeypatch):
+    import cli as cli_mod
+
+    created = {}
+
+    def fake_cli(**kwargs):
+        created["cli"] = _DummyCLI(**kwargs)
+        return created["cli"]
+
+    monkeypatch.setattr(cli_mod, "HermesCLI", fake_cli)
+    monkeypatch.setattr(
+        cli_mod,
+        "build_preloaded_skills_prompt",
+        lambda skills, task_id=None: ("skill prompt", ["hermes-agent-dev", "github-auth"], []),
+    )
+
+    with pytest.raises(SystemExit):
+        cli_mod.main(skills="hermes-agent-dev,github-auth", list_tools=True)
+
+    cli_obj = created["cli"]
+    assert cli_obj.system_prompt == "base prompt\n\nskill prompt"
+    assert cli_obj.preloaded_skills == ["hermes-agent-dev", "github-auth"]
+
+
+def test_main_raises_for_unknown_preloaded_skill(monkeypatch):
+    import cli as cli_mod
+
+    monkeypatch.setattr(cli_mod, "HermesCLI", lambda **kwargs: _DummyCLI(**kwargs))
+    monkeypatch.setattr(
+        cli_mod,
+        "build_preloaded_skills_prompt",
+        lambda skills, task_id=None: ("", [], ["missing-skill"]),
+    )
+
+    with pytest.raises(ValueError, match=r"Unknown skill\(s\): missing-skill"):
+        cli_mod.main(skills="missing-skill", list_tools=True)
+
+
+def test_show_banner_prints_preloaded_skills_once_before_banner():
+    cli_obj = _make_real_cli(compact=False)
+    cli_obj.preloaded_skills = ["hermes-agent-dev", "github-auth"]
+    cli_obj.console = MagicMock()
+
+    with patch("cli.build_welcome_banner") as mock_banner, patch(
+        "shutil.get_terminal_size", return_value=os.terminal_size((120, 40))
+    ):
+        cli_obj.show_banner()
+        cli_obj.show_banner()
+
+    print_calls = [
+        call.args[0]
+        for call in cli_obj.console.print.call_args_list
+        if call.args and isinstance(call.args[0], str)
+    ]
+    startup_lines = [line for line in print_calls if "Activated skills:" in line]
+
+    assert len(startup_lines) == 1
+    assert "Activated skills:" in startup_lines[0]
+    assert "hermes-agent-dev, github-auth" in startup_lines[0]
+    assert mock_banner.call_count == 2
diff --git a/website/docs/user-guide/cli.md b/website/docs/user-guide/cli.md
index fb3c838379..44b42fffca 100644
--- a/website/docs/user-guide/cli.md
+++ b/website/docs/user-guide/cli.md
@@ -27,6 +27,10 @@ hermes chat --provider openrouter  # Force OpenRouter
 # With specific toolsets
 hermes chat --toolsets "web,terminal,skills"
 
+# Start with one or more skills preloaded
+hermes -s hermes-agent-dev,github-auth
+hermes chat -s github-pr-workflow -q "open a draft PR"
+
 # Resume previous sessions
 hermes --continue             # Resume the most recent CLI session (-c)
 hermes --resume <session_id>  # Resume a specific session by ID (-r)
@@ -126,6 +130,17 @@ quick_commands:
 
 Then type `/status` or `/gpu` in any chat. See the [Configuration guide](/docs/user-guide/configuration#quick-commands) for more examples.
 
+## Preloading Skills at Launch
+
+If you already know which skills you want active for the session, pass them at launch time:
+
+```bash
+hermes -s hermes-agent-dev,github-auth
+hermes chat -s github-pr-workflow -s github-auth
+```
+
+Hermes loads each named skill into the session prompt before the first turn. The same flag works in interactive mode and single-query mode.
+
 ## Skill Slash Commands
 
 Every installed skill in `~/.hermes/skills/` is automatically registered as a slash command. The skill name becomes the command: